Vacation rentals in Hailsham

Shepherd’s hut in Lower Dicker

A rustic hut is set on elevated wooden stilts, featuring a front porch with double doors. The structure is surrounded by a well-kept lawn. A fire pit with a grill is positioned in the foreground. Nearby planters add a touch of greenery to the scene.

Secluded Shepherds hut in country location

Relax in the beautiful Sussex countryside. The hut has a hot water shower 2 sinks and a loo and a double bed. Inside the hut you have speakers to listen to your favourite tunes or relax with a book, a game of cards, Jenga or scrabble. Wake up and have a cup of tea or coffee with a view of either the fields or sheep that may be in the vicinity. Bring wellies as the fields are still wet. If you like dogs then mine will most likely come and visit (extremely friendly) No cooking facilities

4.94 out of 5 average rating, 141 reviews

4.83 out of 5 average rating, 107 reviews

A spacious backyard is seen, featuring a well-maintained lawn bordered by stone pathways. A modern house with large windows is visible, complemented by a patio area. Nearby, a shed can be observed, contributing to the functional outdoor space.

Home in Polegate

Delightful 3 bedroom house with sunroom and garden

This stylish modern house is perfect for families. Located within a few miles of Eastbourne and within easy reach of Brighton city centre. Polegate mainline station is close by. Self-contained with 3 generous bedrooms, large sitting room with dining area, fitted kitchen with built in oven & hob, American style fridge freezer, washing machine and dryer, sunroom, bathroom with shower and second ground floor cloakroom. Gas central heating. Private garden & large patio. Car parking for one vehicle.

4.93 out of 5 average rating, 264 reviews

A modern bedroom features a spacious bed with crisp white linens and a gray throw blanket. Nightstands with soft lamps flank the bed, providing gentle illumination. A simple chair and desk are visible, with a door leading to the hallway in the background.

Condo in East Sussex

Entire spacious 2 bed flat Willingdon.king&double

Our modern beautifully presented clean flat is in the heart of Willingdon Village 10 minutes north of Eastbourne. The Village has 2 pubs that serve great food ,Thai restaurant, local post office & is within 15 min walking distance of M&S convenience store located in a BP garage. The flat is approximately 12 min drive from Eastbourne town & seafront. Our flat is within walking distance of the South Downs National Park & Butts Brow. Great for walking.Comfortable Clean & disinfected.King & double

4.91 out of 5 average rating, 254 reviews

Barn in Hellingly

The Barn, Hot tub, projector, Fire Pit, Pizza oven

Our Grade ll Barn is in a quiet countryside spot within driving distance of Eastbourne, Tunbridge Wells, Brighton and Hastings. This unique place has a style all of its own. A spacious home for a romantic getaway or a weekend adventure exploring the local beaches, walks & golf clubs The Barn is equipped with a hot tub, outdoor cinema screen, Ooni pizza oven, firepit/BBQ. We have a driveway which has space for two cars directly outside. *Please note our place is NOT suitable for children.

4.97 out of 5 average rating, 295 reviews

The exterior of the converted barn features a sloped roof with rustic shingles and wooden siding. A gravel driveway leads to the entrance, flanked by planters. Large windows offer views into the open interior, while trees provide a natural backdrop.

Barn in East Sussex

The Cart Lodge a cosy rural hideaway

Situated in a secluded part of our 16th century farm, this detached, south facing cart barn has been converted to a very high standard. In an ideal location overlooking a large duck pond and with distant views to the South Downs. It is a great base for walking the Wealdway or cycling the Cuckoo Trail. Places to explore include Lewes and Eastbourne, 9 miles. Glyndebourne 6 miles. An excellent pub and restaurant is within a ten minute walk along country footpaths. The village shop 2 miles.

4.91 out of 5 average rating, 143 reviews

The two-story country house is surrounded by lush greenery and colorful plants. Large windows invite natural light, while a set of steps leads to the main entrance. The expansive lawn offers a welcoming space to enjoy the outdoors.

Home in Waldron

Spring Farm Sussex

A charming six bedroom country house set in 9 acres of gardens, fields and woodland in the beautiful county of Sussex. The property has a tennis court, indoor heated swimming pool and snooker room. The property has three double bedrooms, a twin bedded room and two further bedrooms which can be configured as twin or double as required. There is a large lawn area as well as three large fields and woodland, in which you are free to amble around and appreciate the beautiful countryside.

4.94 out of 5 average rating, 417 reviews

A charming lodge is shown nestled within a vibrant garden. The exterior features yellow paneling and a brown roof, with large windows offering natural light. Surrounding greenery includes trees and blooming shrubs. A stone patio provides outdoor space, while a separate garden shed is visible nearby.

Home in East Sussex

Self-Contained Garden Lodge

This wonderful lodge is located in the 'Sunshine Coast' of East Sussex. The property is bright, clean and spacious and located at the back of the owner's large garden. It has its own pathway along the side of the owner's house, and is completely self contained and private. However, hosts are nearby at the top of the garden if needed. Beautiful views of the South Downs are visible from The Lodge. It's the perfect place from which to explore Eastbourne and the surrounding area.

4.94 out of 5 average rating, 215 reviews

A spacious barn-style home is showcased against a clear sky, featuring a stone façade and large windows. A grassy lawn extends in front, with shadows cast by trees. Outdoor seating is positioned on a patio area, and a swing set is visible in the background.

Barn in Milton Street

Beautiful barn on the South Downs Way

Beautiful barn, perfect for walkers, also great as a comfortable and spacious base for exploring the local countryside. Local cultural attractions include Glyndebourne, Drusilla's Park, South Downs Way. This spacious artist's home is located right on the South Downs Way, and it is only about an hour and a half walk to the coast at Exceat. There is a tree house for kids, a couple of swing seats for chilling out on, and the Cuckmere runs through the bottom of the garden.

Home in Sovereign Harbour

The living room presents a cozy seating area with a large sofa and two armchairs positioned around a textured area rug. A smart TV is mounted on the wall beside a decorative fireplace. Natural light fills the space through large windows, complemented by soft furnishings.

Cosy 2 bed maisonette with parking by the coast

A cosy and stylish maisonette with one allocated parking space at the front of the property. Visitor parking available opposite the property making this ideal for guests who need their own vehicle to explore beyond Eastbourne. The area is quiet and residential and house is set behind the road giving a bit more privacy for the small garden which is to the front of the property. Please note, there is no back garden.

4.95 out of 5 average rating, 256 reviews

Guesthouse in Herstmonceux

The open-plan living area features a comfortable king-size bed, a television, and a sofa. A rocking chair and a small wooden table are positioned beside large glass doors that provide views of the garden. A patterned rug adds warmth to the space.

Spacious self-contained annex in rural setting

Located in a glorious, peaceful rural setting in an Area of Outstanding Natural Beauty in the High Weald of East Sussex, our annex offers the perfect get-away for a relaxing, peaceful stay in beautiful countryside. Although situated in the depths of the countryside, we are only a 10 minute drive from the market town of Hailsham which has a good selection of shops and supermarkets (Waitrose, Tesco, Asda).

4.98 out of 5 average rating, 378 reviews

Cottage in Boreham Street

The exterior of the cottage showcases charming brickwork and a vibrant green door, surrounded by manicured greenery. Paved pathways lead to the entrance, with a small barrel and decorative plants adding to the inviting atmosphere.

The Stables at Boreham House

The Stables is a converted self-catering cottage in what was the original stables and coach house of Boreham House bed and breakfast and is ideal for couples or families. Inside the cottage the accommodation has been renovated to a very high standard while retaining much of the original character. The cottage is set in beautiful East Sussex countryside within an Area of Outstanding Natural Beauty.

4.98 out of 5 average rating, 148 reviews

4.78 out of 5 average rating, 375 reviews

A charming studio cottage is showcased, featuring a sloped roof and a combination of dark siding and brick foundation. Bright orange flowers are planted in raised garden beds, while a small pathway leads to the entrance. Lush greenery surrounds the property.

Guest suite in Hailsham

Self Contained double\twin en-suite accommodation

Studio, two single beds that are joined to make a king size. Breakfast area with fridge, kettle toaster and small microwave, TV and WiFi, small enclosed garden area. Overnight accommodation ideal for visiting family and friends, work or to explore the local area Twin beds are available for stays of 3 nights or longer. Please let me know at time of booking if you would like twin beds

Popular amenities for Hailsham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Hailsham

5.0 out of 5 average rating, 37 reviews

The exterior of the barn conversion is framed by a garden featuring paved stone pathways and various plants. The entrance showcases wooden double doors surrounded by brick walls and timber accents, while a bench offers a relaxing outdoor seating area.

Barn in Upper Dicker

The Granary

4.97 out of 5 average rating, 66 reviews

A cozy bedroom features a spacious bed dressed in striped bedding. Two neatly folded towels are placed on the bed. Light filters through plantation shutters, illuminating the space. Shelves above the bed display decorative items, contributing to a serene ambiance.

Tiny home in Hellingly

Detached annex with amazing view

4.93 out of 5 average rating, 76 reviews

The cottage entrance is framed by a covered porch with a wooden roof. A brick pathway winds toward the front door, flanked by manicured gardens with low shrubbery. Light filters through trees, enhancing the welcoming appearance of the property.

Cottage in East Sussex

South Downs Listed Country Cottage

4.71 out of 5 average rating, 52 reviews

A brick exterior is highlighted by large glass doors, extending the home's living space outdoors. A circular table with chairs is set on a stone patio, surrounded by lush greenery. The architecture features a steeply pitched roof with decorative gables.

Home in Hailsham

The Walkers Retreat

4.77 out of 5 average rating, 270 reviews

An outdoor dining table is set for a meal, featuring multiple plates and bowls of food. A bottle of champagne stands ready for serving, and an umbrella provides shade. In the background, a large lawn extends with well-maintained greenery, enhancing the outdoor experience.

Home in Chalvington

Entire 3 bed Countryside cottage with large garden

5.0 out of 5 average rating, 5 reviews

Cabin in Hailsham

Lakeside Superior Pet Friendly

4.97 out of 5 average rating, 38 reviews

The exterior of a historic thatched cottage displays a blend of traditional brick and timber framing. Lush greenery and flowering plants surround the entrance, while a charming white picket fence adds to the inviting setting. The structure features prominent chimneys and picturesque windows.

Home in Wilmington

Pond Cottage